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Synlett 2000; 2000(11): 1637-1639
DOI: 10.1055/s-2000-7949
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Rhodium-Catalyzed Addition of Arylboronic Acids to N-Sulfonyl Aldimines

Masato Ueda* , Atsushi Saito, Norio Miyaura
  • *Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan; Fax +81-11-7 06-65 61; E-mail: miyaura@org-mc.eng.hokudai.ac.jp
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Publication Date:
31 December 2000 (online)

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The addition of arylboronic acids, ArB(OH)2, to N-phenylsulfonyl aldimines, RCH=NSO2Ph (R = alkyl, aryl, 1-alkenyl), giving R(Ar)CHNHSO2Ph was carried out at 95 °C in the presence of a rhodium catalyst. [Rh(cod)(MeCN)2]BF4 (3 mol%) was found to be the best catalyst for aryl aldimines and Rh(acac)(coe)2/i-Pr3P for alkyl and 1-alkenyl aldimines. The analogous reactions of arylboronic esters, such as 1,2-ethanediol and 1,3-propanediol ester, yielded the addition products in the presence of two equivalents of Et3N.

arylboronic acids - N-sulfonyl aldimines - rhodium-catalyzed addition - diarylmethylamine

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